Long-Wavelength AIE-Based Fluorescent Probes for Mitochondria-Targeted Imaging and Photodynamic Therapy of Hepatoma Cells.

With this research, we have developed two long-wavelength theranostic probes ( and ) with aggregation-induced emission (AIE)-based properties for image-guided photodynamic therapy (PDT) of hepatoma cells. Introduction of a triphenylamine or carbazole group to a dicyanomethylene-4-pyran dye with long-wavelength fluorescence emission produces the AIE-based probes, which were subsequently modified with triphenyl-phosphonium cation for actively targeting the mitochondria of hepatoma cells. Solution-based experiments show that the probes exhibit a mixed photophysical mechanism of twisted-intramolecular charge transfer and AIE at different aggregation states. The molecular aggregation of the probes also leads to an enhanced ability for oxygen photosensitization, suggesting their potential for PDT of cancer cells. Our subsequent cell-based assays show that the probes localize in the mitochondria of hepatoma cells and the use of light leads to cell death through the intracellular production of reactive oxygen species.